The present invention relates to 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone and novel compositions using 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone to alter, modify, augment, or enhance the flavor and/or aroma of consumable materials or impart flavor and/or aroma to consumable materials.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors and fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials, some of which may be in short supply, and to provide more uniform properties in the finished product. Raspberry juice-like, fruit juice-like, "Damascenone"-like (.beta.-Damascenone, for example, has the structure: ##STR2## tea-like, tobacco-like, apple juice-like, and dried fruit-like aromas and tastes are particularly desirable for many uses in foodstuff flavors, chewing gum flavors, medicinal product flavors, toothpaste flavors and chewing tobacco flavors, particularly in the red berry juice area, tea area, apple juice area, and wine area. Ayyar, Cookson and Kagi do not, however, teach the usefulness of 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone for its organoleptic properties.
Schulte-Elte, U.K. Patent specification No. 1,391,736 discoses and claims a genus of compounds which include 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone and uses of their organoleptic properties but does not specifically teach any specific cyclohexadien compounds per se or their uses for their organoleptic properties. Thus, U.K. Patent specification No 1,391,736 states:
"The compounds to which the invention relates have the formula: ##STR3## wherein: X represents the group: ##STR4##
Floral, fruity, and tobacco aromas with rose notes and hay-like and menthane-like undertones are desirable in several types of perfume compositions, perfumed articles and colognes.
Sweet, dried fruit-like, floral, and woody aromas prior to smoking and sweet and dried fruit aroma characteristics in the mainstream and in the sidestream on smoking, are desirable in smoking tobaccos and smoking tobacco flavoring compositions.
The foregoing aroma and/or taste combinations are only useful if they are compatible with the notes already present in the particular consumable material to be consumed.
3-Hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone, having the structure: ##STR5## has heretofore been indicated by Ayyar, Cookson and Kagi, J. Chem. Soc., Perkin I, 1727 (1975) (Title: "Synthesis of .DELTA.-Damascone [trans-1-(2,6,6-trimethylcyclohex-3-enyl)but-2-en-1-one] and .beta.-Damascenone[trans-1-(2,6,6-trimethylcyclohexa-1,3-dienyl)but-2-en-1 one]") to be useful as an intermediate in preparing "Damascenone" the ".beta." isomer of which has the structure: ##STR6## R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 may be the same or different, and each represents a hydrogen atom or a lower alkyl group having from 1 to 6 carbon atoms; and the ring is saturated or contains one endocyclic double bond in position 1, 2, 3 or 4, or an exocyclic double bond in position 2, or two conjugated double bonds in positions 1 and 3 . . .
The new compounds of formula (I) include the following specific examples:
2,6,6-trimethyl-1-(1,3-dioxo-but-1-yl)-cyclohex-1-ene; PA0 2-methylene-6,6-dimethyl-1-(1,3-dioxo-but-1-yl)-cyclohexane; PA0 2,6,6-trimethyl-1-(3-hydroxy-butan-1-oyl)-cyclohex-1-ene; PA0 2,6,6-trimethyl-1-(3-hydroxy-butan-1-oyl)-cyclohex-2-ene; PA0 2,6,6-trimethyl-1-(2-methyl-1,3-dioxo-but-1-yl)-cyclohex-1ene; PA0 2,6,6-trimethyl-1-(2-methyl-1,3-dioxo-but-1-yl)-cyclohex-2-ene; PA0 2-methylene-6,6-dimethyl-1-(2-methyl-1,3-dioxo-but-1-yl)-cyclohexane; PA0 2,6,6-trimethyl-1(2-methyl-3- hydroxy-butan-1-oyl)-cyclohex-2-ene; PA0 2-methylene-6,6-dimethyl-1-(2-methyl-3-hydroxy-butan-1-oyl)-cyclohexane; PA0 2,6,6-trimethyl-1-(2-methyl-1,3-dihydroxy-but-1-yl)-cyclohex-2-ene; PA0 2,6,6-trimethyl-1-(2-methyl-1,3-dihydroxy-but-1-yl)-cyclohex-1-ene; PA0 2,6,6-trimethyl-1-(1,3-dioxo-but-1-yl)-cyclohexane; PA0 2,6,6-trimethyl-1-(1,3-dihydroxy-but-1-yl)-cyclohexane; PA0 2,6,6-trimethyl-1-(1,3-dihydroxy-but-1-yl)-cyclohex-2-ene; and PA0 2,6,6-trimethyl-1-(1,3-dihydroxy-but-1-yl)-cyclohex-1-ene."
None of the exemplified compounds of U.K. Patent specification 1,391,736 has a chemical structure which can be considered by one having ordinary skill in the art to be even remotely similar to 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone.
A sulfur analogue of 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone, which sulfur analogue has the structure: ##STR7## is disclosed as having useful organoleptic properties in U.S. Pat. No. 3,979,422 issued on The organoleptic properties of the compound having the structure: ##STR8## are different in kind from the organoleptic properties of 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone having the structure: ##STR9## and, the properties of 3-hydroxy-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-1-butanone are unexpectedly and unobviously advantageous insofar as the taste and aroma nuances are concerned and further insofar as the intensity and lasting power is concerned.